Potassium Carbonate → HCID 57095368, compound

HRID 2287998Notes

Reaction equation

HRID 2287998 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([S:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([NH:18][C@@H:19]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH:20]([CH3:22])[CH3:21])(=[O:17])=[O:16])=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1.Cl.Cl[CH2:32][CH2:33][N:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:1][C:2]1[CH:3]=[C:4]([S:8][C:9]2[CH:10]=[CH:11][C:12]([S:15]([N:18]([CH2:32][CH2:33][N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)[C@@H:19]([C:23]([O:25][C:26]([CH3:27])([CH3:29])[CH3:28])=[O:24])[CH:20]([CH3:22])[CH3:21])(=[O:17])=[O:16])=[CH:13][CH:14]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)2×HCID 53937076HCID 53937076, compound

Product 1

HCID 57095368HCID 57095368, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
63 °C

Procedure

To a solution of N-[[4-[(3-methylphenyl)thio]phenyl]sulfonyl]-D-valine, 1,1-dimethylethyl ester, from Example 1c (3.96 g, 9.08 mmol) in 30 mL DMF was added 4-(2-chloroethyl)-morpholine hydrochloride (5.07 g, 27.2 mmol) and K2CO3 (3.76 g, 27.2 mmol). The solution was heated to 63° C. for 24 hours. Additional K2CO3 (1.25 g, 9.08 mmol) and 4-(2-chloroethyl)-morpholine hydrochloride (1.69 g, 9.08 mmol) was added and the mixture heated for an additional 24 hours at 63° C. The mixture was then partitioned between ethyl acetate and H2O, and the organic was washed with sat'd NaCl (3×30 mL) and dried over MgSO4. After concentration in vacuo, the residue was purified by flash chromatography (20:80 hexane/EtOAc) to afford N-[[4-[(3-methylphenyl)thio]phenyl]sulfonyl)-N-[2-(4-morpholinyl)ethyl]-D-valine, 1,1-dimethylethyl ester, as a white solid (5.21 g): MS MH+ calc'd for C28H41N2O5S2 : 549, found: 549. HRMS calc'd for C28H41N2O5S2 : 548.2379; found: 548.2384.

Workup

  1. temperaturethe mixture heated for an additional 24 hours at 63° C
  2. customThe mixture was then partitioned between ethyl acetate and H2O
  3. washthe organic was washed with sat'd NaCl (3×30 mL)
  4. dry with materialdried over MgSO4
  5. concentrationAfter concentration in vacuo
  6. customthe residue was purified by flash chromatography (20:80 hexane/EtOAc)

Sources & evidence

ORD record
ord-2814f0cc3dec4d1883c2e1af0c95649d
Source dataset
uspto-grants-2000_07
Patent number
US06087359

Reaction notes

Loading…